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Aye yi yi. I have seen this often, and it never ends up pretty. OK, one time it did but they got married and didn't tell a soul, not mom, not best friend, not even the dog. The only evidence was the Mil ID in her wallet (hidden) and she only pulled it out at the PX, or Commissary etc. She did tell everyone 10 years later. "Loose lips sink ships" and it's sooo hard to keep the trap shut in these matters. Why? Although ppl say they don't care, they do, and at the last minute they will start to "bail" on you and will say snarky things like "what's the big deal, they're already married" and it really takes away from your day. Plus, if you tell the BFF's they will get you presents and then a year later ppl just feel like "I've already given them a gift, I don't need to go to this one". I know they say they will, but I've seen so many of these go sour. To the point that the Bride and groom just say "screw it, we'll forget the big wedding".
Can you just speed things up and do it in Sept. w/o the best man of choice? I would personally go that route. Men understand and are cool with this.
If you are doing it just for the Tricare and his BAH, you need to "worst case scenario" it and say who is the best person, you or his mom, to move out to Walter Reed for a year or more if he's in rehab and comes home w/o limbs etc. This is just too serious for me to sugar coat it for you. Sorry.
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